Stereoselective functionalization of pyrrolidinone moiety towards the synthesis of salinosporamide A
2012 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 68, no 32, 6504-6512 p.Article in journal (Refereed) Published
An important feature of the synthesis of salinosporamide A. a potent proteasome inhibitor, is the establishment of the quaternary stereocenter at C3. A new route has been developed based on the methylation of a functionalized pyrrolidinone. Direct methylation reaction led to the unwanted diastereomer: however, by means of a Corey-Chaykovsky reaction followed by LiAlH4 epoxide opening, the desired alcohol was obtained. The pyrrolidinone was elaborated through a key allylation reaction between a tertiary allyltitanium reagent and an aldehyde bearing a spiroketal moiety in alpha-position.
Place, publisher, year, edition, pages
2012. Vol. 68, no 32, 6504-6512 p.
Salinosporamide, Hoppe allylation, Pyrrolidinone, Methylation reaction, Corey-Chaykovsky reaction
IdentifiersURN: urn:nbn:se:su:diva-80630DOI: 10.1016/j.tet.2012.05.103ISI: 000306267800014OAI: oai:DiVA.org:su-80630DiVA: diva2:556466
FunderSwedish Research Council